Methylamine → 5-Bromo-3-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 1959453노트

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HRID 1959453 반응식
[Br:1][C:2]1[N:3]=[C:4]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20]Br)=[CH:16][CH:15]=3)=[N:12][N:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:28][NH2:29]>O1CCCC1.O>[Br:1][C:2]1[N:3]=[C:4]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][NH:29][CH3:28])=[CH:16][CH:15]=3)=[N:12][N:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 6329MethylamineHCID 10340Sodium CarbonateHCID 580704675-Bromo-3-(5-(4-(bromomethyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

생성물 1

HCID 594716885-Bromo-3-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine수율 97%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
60 °C

실험 절차

A suspension of 5-bromo-3-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-amine (2 g, 4.9 mmol) and Na2CO3 (1.55 g, 14.60 mmol) in tetrahydrofuran (30 mL) was treated with methanamine (3.6 mL of 2 M, 7.3 mmol) in THF. The reaction mixture was heated at 60° C. for 1 h. The reaction was cooled, diluted with water and the organic layer was extracted with dichloromethane. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to yield 5-bromo-3-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (1.7 g, 97%) as a yellow solid, which was used without purification in the next step. LC/MS m/z 363.5 [M+H]+.

후처리

  1. temperatureThe reaction was cooled
  2. extractionthe organic layer was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-466d8a6958a74ecf91a18a25395c72e8
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410112B2

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